CN1917761B - Fungicidal compositions comprising pyridylethylbenzamide derivatives and compounds capable of inhibiting methionine biosynthesis - Google Patents

Abstract

A composition comprising at least a pyridylethylbenzamide derivative of general formula (I) (a) and a compound capable of inhibiting the methionine biosynthesis (b) in a (a)/(b) weight ratio of from 0.01 to 20. A composition further comprising an additional fungicidal compound. A method for preventively or curatively combating the phytopathogenic fungi of crops by using this composition.

Description

Fungicidal compositions comprising pyridylethylbenzamide derivatives and compounds capable of inhibiting methionine biosynthesis

The present invention relates to novel fungicidal compositions comprising pyridylethylbenzamide derivatives and compounds capable of inhibiting the biosynthesis of methionine. The invention also relates to methods of combating or controlling phytopathogenic fungi by applying such compositions to loci that are infected or susceptible to infection.

International patent application WO 01/11965 generally discloses a number of pyridylethylbenzamide derivatives. The possibility of one or more of these many pyridylethylbenzamide derivatives being combined with known fungicidal products to enhance fungicidal activity is generally disclosed without giving any specific examples or biological data.

In the field of agriculture, in order to significantly avoid or control the development of resistant strains to the active ingredients or mixtures of known active ingredients used by farmers, while at the same time reducing the dose of chemicals dispersed in the environment as much as possible, the reduction of handling cost, there has been interest in using new mixtures of pesticides that exhibit synergistic effects.

The inventors have now found some novel fungicidal compositions having the above-mentioned characteristics.

Accordingly, the present invention relates to a composition comprising:

a) pyridylethylbenzamide derivatives of the general formula (I) and N-oxides of 2-pyridine,

In the formula:

- p is an integer equal to 1, 2, 3 or 4;

-q is an integer equal to 1, 2, 3, 4 or 5;

- Each substituent X is independently selected from halogen, alkyl or haloalkyl;

-Each substituent Y is independently selected from halogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy, alkylthio, dialkylamino, acyl, cyano, ester , hydroxy, aminoalkyl, benzyl, haloalkoxy, halosulfonyl, halothioalkyl, alkoxyalkenyl, alkylsulfonylamido, nitro, alkylsulfonyl, phenylsulfonyl or Benzylsulfonyl; and

b) compounds capable of inhibiting the biosynthesis of methionine;

wherein the weight ratio of (a)/(b) is 0.01 to 20.

In the narrative of the present invention:

- halogen means chlorine, bromine, iodine or fluorine;

- both the alkyl and acyl groups are present as straight or branched molecules containing 1 to 10 carbon atoms, preferably 1 to 7 carbon atoms, more preferably 1 to 5 carbon atoms;

- Both alkenyl or alkynyl groups are present as straight or branched molecules containing 2 to 10 carbon atoms, preferably 2 to 7 carbon atoms, more preferably 2 to 5 carbon atoms.

The compositions according to the invention provide a synergistic effect. This synergistic effect reduces the dispersal of chemicals into the environment and reduces the cost of fungicidal treatments.

In the description of the present invention, the term "synergistic effect" is based on the calculation of the synergistic and antagonistic responses of herbicide compositions entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations" Weeds, (1967), 15, No. 20- The 22-page essay is defined by Colby.

The equation mentioned in the above article:

$\mathrm{<span\; class="notranslate">\; E.</span>}<span\; class="notranslate">\; =</span>\mathrm{<span\; class="notranslate">\; x</span>}<span\; class="notranslate">\; +</span>\mathrm{<span\; class="notranslate">\; the\; y</span>}<span\; class="notranslate">\; -</span>\frac{\mathrm{<span\; class="notranslate">\; x</span>}<span\; class="notranslate">\; *</span>\mathrm{<span\; class="notranslate">\; the\; y</span>}}{\mathrm{<span\; class="notranslate">\; 100</span>}}$

where E represents the expected percentage inhibition of disease by a combination of two fungicides at a specific dose (e.g., equal to x and y, respectively), x is the observed percentage inhibition of disease at a specific dose (equal to x) of Compound (I), and y is the observed percent inhibition of disease at a specific dose (equal to y) of compound (II). Synergy is indicated when the percent inhibition of the observed combination exceeds E.

The composition according to the invention comprises a pyridylethylbenzamide derivative of general formula (I). Preferably, the present invention relates to a composition comprising pyridylethylbenzamide derivatives of general formula (I), wherein the following different features can be selected individually or in combination:

- Regarding p, p is 2;

- Regarding q, q is 1 or 2. More preferably, q is 2;

- Regarding X, each X is independently selected from halogen or haloalkyl. More preferably, each X is independently selected from a chlorine atom or a trifluoromethyl group;

- Regarding Y, each Y is independently selected from halogen or haloalkyl. More preferably, each Y is independently selected from a chlorine atom or a trifluoromethyl group;

More preferably, the pyridylethylbenzamide derivative of general formula (I) present in the composition of the present invention is:

-N-{2-[3-Chloro-5-(trifluoromethyl)-2-pyridyl]ethyl}-2-trifluoromethylbenzamide (Compound 1);

-N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl}-2-iodobenzamide (compound 2) or

-N-{2-[3,5-Dichloro-2-pyridyl]ethyl}-2-trifluoromethylbenzamide (Compound 3).

More preferably, the pyridylethylbenzamide derivative of general formula (I) present in the composition of the present invention is N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridine Base] ethyl}-2-trifluoromethylbenzamide (compound 1).

The composition according to the invention comprises a compound capable of inhibiting the biosynthesis of methionine. Preferably, the present invention relates to a composition comprising a compound capable of inhibiting the biosynthesis of methionine selected from the group consisting of cyprodinil, azimethanil and pyrimethanil. Preferred is pyrimethanil.

The composition according to the invention comprises (a) at least one pyridylethylbenzamide derivative of general formula (I) and (b) a compound capable of inhibiting the biosynthesis of methionine, (a)/( The weight ratio of b) is 0.01 to 20; preferably 0.05 to 10; more preferably 0.1 to 5.

The compositions according to the invention may further comprise at least one other different fungicidally active ingredient (c).

The fungicidal active ingredient (c) may be selected from the group consisting of penconazole, azoxystrobin, (Z)-N-[α-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoro Methyl)benzyl]-2-phenylacetamide, 6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one, benalaxyl, benomyl, benomyl Amine (benthiavalicarb), biphenyl, bisbentriazole, blasticidin, boscalid, borax, furconazole, pyrithrimol sulfonate, sec-butylamine, calcium polysulfide, captafol , captan, phenylcarbamate, wilting, cyproamide, acarid, chlorothalonil, ethylclonil, copper hydroxide, copper octoate, copper oxychloride, copper sulfate, oxychloride Copper, Cyazofamid, Cymoxanil, Cycloconazole, Cyprodinil, Diamron, Profencarb, Benflusulfonamide, Dichlorophen, Triconazole Triconazole, Diclofenac, Pyridoxil, Nicloramine, Dimethocarb, Difenoconazole, Difenzoquat metilsulfate, Difenzoquat, Fluoxamethanil, Dimethylen, Dimethomorph, Difenazole, Mite Tong, Xiaomaicap, diphenylamine, dicyanoanthraquinone, dodecacyclomorpholine, dodecacyclomorpholine acetate, dodine, difenfo-fos, oxaconazole, ethaboxam, pyrimethol, acetylene Oxyquinoline, Etoconazole, Tribendazim, Methafluconone, Midafluxone, Chlorpyrimidinol, Nibendazole, Mefuramide, Fenhexamid, Seed Dressing, Cyanoxanil, Fenpropidin , fenpropimorph, triphenyltin (fentin), triphenyltin hydroxide (fentin hydroxide), triphenyltin acetate (fentin acetate), ferbam, aziprodil hydrazone, fluazinam, fludioxonil, Flupronil, fluoxastrobin, fluquinazole, flusilazole, sulfanil, flunamide, fluoxazol, folpet, formaldehyde, fosetyl, aluminum triethylphosphonate, Guazatine, furaxyl, furamet, biguanide, guazatine acetates, hexachlorobenzene, hexaconazole, 8-hydroxyquinoline sulfate, hydroxyquinoline potassium sulfate, bad mold Imazalil, imazalil sulfate, imazalil, imidazole, biguanidine octylamine, biguanidine octylamine acetate, cloconazole, isofridazine, iprodione, iprovalicarb (iprovalicarb), rice blast Ling, kasugamycin, kasugamycin hydrochloride hydrate (kasugamycin hydrochloride hydrate), kresoxim-methyl, mancocopper, mancozeb, maneb, azurprodil, promethamine, mercuric chloride, mercuric oxide, Calomous chloride, metalaxyl, high-efficiency metalaxyl, metam-sodium, metam, metconazole, sulfacarb, methyl isothiocyanate, dysonite, benzene Oxystrobin, amycin, myclobutanil, sodium dyson, bis(dimethyldithiocarbamate) nickel, phthastrobin, fluoxetine alcohol, octhilone, furamide, oleic acid, oxa Dexterin, quinoline copper, oximidazole fumarate, oxidized arbor, rice blastyl, penconazole, pentocuron, pentachlorophenol, sodium pentachlorophenolate, month Pentachlorophenyl laurate, phenylmercury acetate, sodium 2-phenylphenate, 2-phenylphenol, phosphorous acid, tetrachlorophthalide, picoxystrobin, phylloxine, polyoxinspolyoxin B (polyoxinspolyoxin B) , polyoxin, polyoxin, allyl benzothiazole, prochloraz, procymidone (procymidone), propamocarb hydrochloride (propamocarb hydrochloride), propamocarb, propiconazole, propamocarb, procymidone Conazole (prothioconazole), pyraclostrobin (pyraclostrobin), pyritropin, barnyard grass, acetoxime, pyrimethanil, pyroquinone, phenoxyquinoline, pentachloronitrobenzene, silthiocarbam, Silfluzole, spirulina, sulfur, tar, tebuconazole, tetrachloronitrobenzene, tetrafluconazole, thiabendazole, thifuramide, thiophanate-methyl, thiram, tolclofos-methyl , Tobendazole, triadimefon, triadiazole, imidazosin, tricyclazole, tridemorph, trifloxystrobin, fluconazole, azinamine, fenconazole, validamycin, vinyl sclerotia Lee, Zinc, Zirmet and Benzalk.

Preferably, the fungicidal active ingredient (c) is selected from the group consisting of captan, propenezin, fenhexamid, trifloxystrobin, tofluafenazole, iprodione, procymidone and chlorothalonil.

When the third active ingredient (c) as defined above is present in the composition, the compound is present in an amount of (a):(b):(c) in a weight ratio of 1:0.01:0.01 to 1:20:20 ; The proportions of compound (a) and compound (c) vary independently. Preferably, the weight ratio of (a):(b):(c) may be from 1:0.05:0.05 to 1:10:10.

The following compounds are given to illustrate non-limiting examples of the present invention: compound 1 and cyprodinil, compound 1 and azoxystrobin, compound 1 and pyrimethanil, compound 2 and cyprodinil, compound 2 and azoxystrobin , compound 2 and pyrimethanil, compound 3 and pyrimethanil, compound 3 and pyrimethanil, compound 3 and pyrimethanil.

The compositions according to the invention may also comprise other additional components, such as agriculturally acceptable carriers, carriers or fillers.

In the context of the present invention, the term "support" denotes a natural or synthetic organic or inorganic material, which is combined with an active substance to facilitate its application, in particular to plant parts. Therefore, this support is generally inert and should be agriculturally acceptable. The support can be solid or liquid. Examples of suitable supports include clays, natural or synthetic silicates, silicon dioxide, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and their derivatives. Mixtures of such supports may also be used.

The composition may also contain other components. In particular, the composition may also comprise a surfactant. The surfactant can be an ionic or nonionic emulsifier, dispersant or wetting agent or a mixture of such surfactants. For example, polyacrylates, lignosulfonates, phenolsulfonates or naphthalenesulfonates, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines, substituted phenols (especially alkylphenols or aryl phenol), salts of sulfosuccinates, taurine derivatives (especially alkyl taurates), phosphate esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyols, and compounds containing sulfuric acid, Derivatives of the above compounds with sulfonic acid and phosphoric acid functional groups. The presence of at least one surfactant is generally essential when the active substance and/or the inert support is water insoluble, and when the vehicle for application is water. Preferably, the content of the surfactant is between 5% and 40% by weight based on the weight of the composition.

Additional components may also include, for example, protective colloids, adhesives, thickeners, thixotropes, penetrants, stabilizers, chelating agents. More generally, the active substances may be mixed with any solid or liquid additives by conventional formulation techniques.

In general, the compositions according to the invention may contain from 0.05% to 99% by weight of active substance, preferably from 10% to 70% by weight.

The composition of the present invention can be used in various forms, such as aerosol dispersion, microcapsule suspension, cold spray, dustable powder, emulsified oil, oil-in-water emulsion, water-in-oil emulsion, microcapsule particle, fine particle Suspensions for seed treatment, compressed gas (depressurized) preparations, gas generants, granules, thermal mist, macrogranules, microgranules, oil-dispersible powders, oil-miscible suspensions, oil-miscible solvents , pastes, plant sticks, dry seed treatment powders, pesticide-coated seeds, soluble liquids, soluble powders, seed treatment solutions, suspensions (flowable concentrates), ultra-low volume (ulv) liquids, Ultra-low volume (ulv) suspension concentrates, water dispersible granules or tablets, water dispersible powders for slurry treatment, water soluble granules or tablets, water soluble powders for seed treatment, and wettable powders.

These include not only compositions which are readily applied to the plants or seeds to be treated by suitable equipment, such as spraying or dusting equipment, but also concentrated commercial compositions which must be diluted before application to crops.

The fungicidal composition of the present invention can be used for the treatment or prevention of phytopathogenic fungi which control crops. Therefore, according to other aspects of the present invention, there is provided a method of preventing or therapeutically controlling phytopathogenic fungi in crops, which method is characterized in that the above-mentioned fungicidal composition is applied to seeds, plants and/or fruits of plants or plants In the soil where it is growing or needs to grow.

The compositions for combating phytopathogenic fungi of agricultural crops comprise an effective and non-phytotoxic amount of active substances of the general formula (I).

The expression "effective and non-phytotoxic amount" means that the amount of the composition of the present invention is sufficient to control or destroy the fungus present or prone to occur on the crop, and the amount does not cause any observable phytotoxicity to the crop symptom. Depending on the fungus to be combated or controlled, the type of crop, the climatic conditions and the compounds contained in the fungicidal composition of the invention, the amount of the composition used can vary within wide limits.

The amount used can be determined by systematic field trials, which is within the ability of those skilled in the art.

The treatment method according to the invention is used for the treatment of propagation material such as tubers or rhizomes, and also seeds, seedlings or selected shoots and plants or selected plants. This treatment method can also be used to treat roots. The treatment method according to the invention is also useful for treating air-exposed parts of plants such as trunks, stems or stalks, leaves, flowers and fruits of the plants concerned.

Among the plants which can be protected by the method according to the invention are cotton; flax; vines; fruit crops such as Rosaceae sp. almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp. .), Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (such as banana trees and plantins), Rubiaceae sp.), Theaceae sp., Sterculiceae sp., Rutaceae sp. (eg lemons, oranges and grapefruit); leguminous crops such as Solanaceae sp. ( For example, tomato), Liliaceae sp., Asteraceae sp. (e.g. lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp. (e.g. peas), Rosaceae sp. (e.g. strawberries); large crops; such as Graminae sp. (e.g. maize, cereals such as wheat, rice, barley, and triticale), Asteraceae sp. (e.g. sunflower), Cruciferae sp. (e.g. canola), Papilionaceae sp. (e.g. soybean), nightshade Solanaceae sp. (e.g. potato), Chenopodiaceae sp. (e.g. beetroot); horticultural and forest crops; and genetically modified homologues of these crops.

Among the possible diseases of these plants and of these plants protected by the method of the invention include:

- Wheat, for the control of the following seed diseases: fusaria (Microdochium nivale and Fusarium roseuum), stinking smut (T. Tilletia caries), Tilletia controversa or Tilletia indica), septoria disease (Septoria nodorum) and loose smut ( loose smut);

- Wheat, control of the following diseases on the air-exposed parts of the plant: cerealeyespot (Tapesia yallundae, Tapesia acuiformis), take-all (Gaeumannomyces graminis), hairy root wilt (foot blight) (F. culmorum, F. graminearum), black speck (Rhizoctonia cerealis), powdery mildew ( graminearum (Erysiphe graminis formaspecie tritici), rust (Puccinia striiformis and Puccinia recondita) and ascosporidium (Septoria tritici ( Septoria tritici) and Septoria solani);

- Wheat and barley to control bacterial and viral diseases such as barley yellow mosaic;

- Barley, for the control of the following seed diseases: net blotch (Pyrenophora graminea, Pyrenophora teres and Cochliobolus sativus), loose smut (Ustilago nuda) and Fusarium (M.

- Barley, for the control of the following diseases on the air-exposed parts of the plant: Cereal ring spot (Tapesiayallundae), reticular spot (Torosclerotia and Helicosporum graminis), powdery mildew (Erysiphe graminis forma specie hordei)), dwarf leaf rust (Puccinia hordei) and leaf blotch (Rhynchosporium secalis);

- Potatoes, control of tuber diseases (especially Helminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusarium solani) ), mildew (Phytopthora infestans) and certain viruses (virus Y);

- Potatoes, to control the following foliar diseases: early bright (Alternaria solani), Phytophthora infestans;

- Cotton, for the control of the following diseases in young plants grown from seeds: damping-off and collar rot (Rhizogonia solani, Fusarium oxysporum) and black root rot blackroot rot (Thielaviopsis basicola);

-Protein producing crops, such as peas, for the control of the following seed diseases: anthracnose (Ascochyta pisi, Mycosphaerella pinodes), Fusarium (Fusarium oxysporum), Botrytis cinerea (Botrytis cinerea) and mildew (Peronospora pisi);

- control of the following seed diseases in oil-bearing crops, such as rapeseed: Phomalingam, Alternaria brassicae and Sclerotias clerotiorum;

- Corn, control of seed diseases: (Rhizopus sp., Penicillium sp., Trichoderma sp., Aspergillus sp. and Gibberella fujikuroi );

- flax, control of seed diseases: Alternaria linicola;

- forest trees, damping-off control (Fusarium oxysporum, Rhizoctonia solani);

- Rice, to control the following diseases on air-exposed parts: blast disease (Magnaporthe grisea), bordered sheath spot (Rhizoctonia solani);

- Leguminous crops, control of the following diseases on seed or young plants grown from seed: damping-off and neck rot (Fusarium oxysporum, Fusarium pink, Rhizoctonia solani, Pythium sp.) ;

- leguminous crops for the control of the following diseases on air-exposed parts: gray mold (Botrytis sp.), powdery mildew (especially Erysiphe cichoracearum), cocklebur (Sphaerotheca fuliginea) and tartar Leveillula taurica), Fusarium (Fusarium oxysporum, Fusarium pink), Leaf spot (Cladosporium sp.), Alternaria leaf spot (Chain Alternaria sp.), Anthracnose (Colletotrichum sp.), Septoria leaf spot (Septoria sp.), Black spot (Rhizoctonia solani), mildews (e.g. Bremia lactucae, Peronospora sp., Pseudoperonospora sp., Phytophthora sp.);

- Fruit trees, to control the following diseases on parts exposed to the air: monilia disease (Monilia fructigenae, M. laxa), scab (apple black star fungus (Venturia inaequalis)), powdery mildew (Podosphaera leucotricha);

- Vine plants, controlling plant diseases: especially gray mold (Botrytis cinerea), powdery mildew (Uncinula necator), black rot (Guignardia bidwelli) and mildew (Vitis vinifera) Plasmopara viticola);

- Beetroot, control of the following diseases on air-exposed parts: cercosporablight (Cercospora beticola), powdery mildew (Erysiphebeticola), leaf spot (Ramularia beticola)).

The fungicidal compositions of the present invention may also be used against fungal diseases which tend to grow on or in wood. The term "wood" refers to all kinds of wood, and all processed materials of such wood used in construction, such as solid wood, high-density wood, laminated wood and plywood. The method of treating wood of the present invention essentially comprises: contacting with one or more compounds of the present invention or a composition of the present invention; this includes for example direct application, spraying, dipping, infusion or any other suitable means.

The fungicidal compositions of the invention may also be used for the treatment of genetically modified organisms using the compounds of the invention or the agrochemical compositions of the invention. A genetically modified plant is one whose genome has stably incorporated a heterologous gene encoding a protein of interest. "Heterologous gene encoding a protein of interest" mainly refers to a gene that imparts new agronomic properties to transformed plants, or refers to a gene that improves the agronomic properties of transformed plants.

The active materials generally used in the treatment method according to the invention are generally and advantageously applied in doses of 10 to 2000 g/ha, preferably 20 to 1500 g/ha, for application in foliar treatment. In the case of seed treatment, the active substances are usually and advantageously applied at a dosage of 1 g/100 kg of seed to 200 g/100 kg of seed, preferably of 2 g/100 kg of seed to 150 g/100 kg of seed. It should be clearly understood that the dosages specified above are only illustrative examples of the invention. A person skilled in the art knows how to adjust the applied dosage according to the nature of the crop to be treated.

The compositions of the invention may also be used for the preparation of compositions useful for the treatment or prevention of fungal diseases in humans and animals, such as mycoses, dermatoses, mosses and candidiasis or caused by Aspergillus or Candida species (Candida spp.) such as Aspergillus fumigatus or Candida albicans (Candida albicans).

The invention will now be illustrated with the following examples:

Example 1: Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl}-2-trifluoromethylbenzoyl A mixture of amine (compound 1) and cyprodinil against Erysiphe graminis wheat-specific (Erysiphe graminis f.sp.graminis) potency

The active ingredients tested were prepared by earthenware homogenization in a mixture of acetone/tween/water. This suspension is then diluted with water to obtain the desired concentrate of active material.

Wheat plants (variety Audace) were placed in starter cups, sown onto a 50/50 peat soil-pozzolana substrate and grown at 12 °C at the 1-leaf stage (10 cm tall) by The plants are treated by spraying the aforementioned aqueous suspension.

As a control, the plants are treated with an aqueous solution not containing active material.

After 24 hours, the plants were contaminated by dusting them with spores of Erysiphe graminis f. sp. tritici, by using the diseased plants.

Grading was performed 7 to 14 days after contamination, compared to control plants.

The table below summarizes the results obtained when Compound 1 and cyprodinil were tested alone and as a mixture in a 16:1 weight ratio.

According to the Colby method, a synergistic effect was observed for the tested mixtures.

Example 2: Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl}-2-trifluoromethylbenzene Formyl Efficacy of a mixture of amine (compound 1) and pyrimethanil against Botrytis cinerea

The formulated compound (concentrated suspension) is diluted with water to obtain the desired concentrate of active material, the gherkin plants (Petit Vert de Paris variety) are placed in starter cups and sown on a 50/50 peat soil-pozzolan substrate , and grown at 18-20° C., the plants were treated at the cotyledon Z11 stage by spraying the above-mentioned aqueous suspension. As a control, the plants were treated with an aqueous solution not containing the active material.

After 24 hours, the plants were contaminated by depositing droplets of an aqueous suspension of Botrytis cinerea spores (150000 spores/ml) on the upper surface of the leaves. Spores were collected from 15-day-old cultures and suspended in a nutrient solution consisting of:

-20 g/l gelatin

-50 g/l sucrose

-2 g/l NH ₄ NO ₃

- 1 g/l KH ₂ PO ₄ .

Contaminated gherkin plants are kept for 5/7 days in a climate chamber at 15-11° C. (day/night) and 80% relative humidity. Grading (% potency) was carried out 5 to 7 days after contamination, compared to control plants.

The table below summarizes the results obtained when tested compound 1 and pyrimethanil were used alone and as mixtures in different weight ratios.

According to the Colby method, a synergistic effect was observed for the tested mixtures.

Example 3: Containing N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl}-2 trifluoromethylbenzoyl Efficacy of a mixture of amine (compound 1) and azoxystrobin against Erysibacter graminearum hordeum specification

The active ingredients tested were prepared by earthenware homogenization in a mixture of acetone/Tween/water. This suspension is then diluted with water to obtain the desired concentrate of active material.

Barley plants (Express variety) were placed in starter cups, sown onto a 50/50 peat soil-pozzolan substrate and grown at 12°C at the 1-leaf stage (10 cm high) by spraying the above aqueous suspension. Treat the plant.

As a control, the plants are treated with an aqueous solution not containing active material.

After 24 hours, the plants were contaminated by dusting them with spores of Erysipha graminearum hordeum specific, using diseased plants.

Grading was performed 7 to 14 days after contamination, compared to control plants.

The table below summarizes the results obtained when tested compound 1 and azoxystrobin were used alone and as a 1:1 mixture by weight.

According to the Colby method, a synergistic effect was observed for the tested mixtures.

Claims (3)

1. A synergistic composition comprising: a) N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl}-2-trifluoromethylbenzamide; and b) a compound selected from the group consisting of cyprodinil, pyrimethanil or pyrimethanil that inhibits the biosynthesis of methionine; wherein the weight ratio of (a)/(b) is 0.1 to 20. 2. The composition of claim 1, further comprising an agriculturally acceptable substance selected from a carrier and a surfactant. 3. A method for preventive or therapeutic control of phytopathogenic fungi in crops, characterized in that, the composition as claimed in claim 1 or 2 is applied to plant seeds and/or plant fruits effectively and in non-phytotoxic amounts Or in the soil where the plant is growing or needs to grow.